Methylketobutanol.



UNITED STATES PATENT OFFICE.

GEORG M E'LING AND. HUGO KfiHLEE, or ELE EEELD, GERMANY, ASSIGNORS '10 FARBENFABRIKEN VORM. FRIEDR. BAYER & 00., or ELBERFELD, GERMANY, A-

CORPORATION OF GERMANY.

METHYLKETO BUTANOL.

No Drawing.

Specification of Letters Patent. Patented J an. 17, 1911. Application filed December 21,..1909. Serial No. 534,348.

(Specimens) To all whom it may concern:

Be it known that we, GEORG MERLING, professor of chemistry, doctor of philosophy, and HUGO -K6HLER, doctor of philosophy, citizens of the Germain Empire, residing at- Elberfeld, Germany, have invented new and useful Improvements in Methylketobutanol, of which the following is a specification.

This application relates to the manufacture and production of methylketobutanol while in our copending application Serial No. 533699, filed December 17, 1909, we describe the whole class of ketone alcohols. The new product is obtained by treating ethylmethylketone with formaldehyde or compounds capable of generating formaldehyde in the presence of alkaline condensing agents exercising a mild action on the components to be condensed. Such condensing agents are e. g. sodium or potassium carbonate, magnesium carbonate or oxid, bisodium phosphate, borax, etc.

In order toillustrate the new process more fully the following example is given, the parts being by weight: A mixture of 100 parts of ethylmethylketone with 30 arts of a 35 per cent. formaldehyde is mixed vt'ogether with an aqueous solution of 1 part of potassium carbonate in 2 parts of water. Themixture is allowed to stand for about 40 hours while shaking it from time to time until in a test-portion diluted with water formaldehyde can no longer be detected. To carry out this test some drops of an aqueous solution of acetate of anilin are added to the diluted liquid which is then allowed to stand for 15 minutes. If after this time no precipitation or clouding due to the formation of methylene anilin is observed, the liquid is free from formaldehyde. The potash solution is removed by means of a separatoryfunnel, the remaining liquid is carefully neutralized with dilute hydrochloric acid or it is acidulated with tartaric acid, the potas-' sium chlorid or tartrate is filtered off and the filtrate is distilled in vacuo, the vessel being heatedon a water bath. Methylethylketone passes over, while the new methylketobutanol:

mm. pressure. The pure methylketobutanol boils at 90 to 91 C. at 18 mm. pressure. It is av limpid colorless oil soluble in water, alcohol and ether. On being boiled with acetic acid anhydrid it is converted into the acetyl compound CH3- co-cH- 0H, 0 cocnt,

a limpid, stable oil boiling at 90 to 92 C. at 16 mm. pressure. The formation of the new product takes probably place according to the following formula:

' OH, on, co (in, cn o 3 -CH5-COfIH-CH,OH The methylketobutanol is a valuable intermediate product for the production of pharmaceutical products or other valuable bodies. 7

We claim:

The herein described methylketobutanol, obtainable by reacting upon methylethylketone with formaldehyde, which is a limpid colorless oil boiling at 90-91 C. at 18 mm. pressure, soluble in water, alcohol, ether and benzole, being converted into the acetyl compound on being boiled with acetic acid anhydrid which acetyl compound is a limpid 011 boiling at 9092 C. at 16 mm. pressure, substantially as described.

In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses. GEORG MERLING. [L.s.]

HUGO KCHLER. [L.s.] Witnesses: Y

O'rro Kome,

CnAs. J. Wmen'r. 

